HCID 68982294, compound → 5-Amino-2-(2-pyrrolidin-1-yl-ethoxy)-benzoic acid methyl ester

HRID 1820860Notes

Reaction equation

HRID 1820860 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([N+:19]([O-])=O)[CH:8]=[CH:9][C:10]=1[O:11][CH2:12][CH2:13][N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:4]>CO.[H][H].[Ni]>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([NH2:19])[CH:8]=[CH:9][C:10]=1[O:11][CH2:12][CH2:13][N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:4]

Participants

5

Reactant 1

HCID 68982294HCID 68982294, compound

Product 1

HCID 575164935-Amino-2-(2-pyrrolidin-1-yl-ethoxy)-benzoic acid methyl ester

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

1.65 g (5.61 mmol) of 3-methoxycarbonyl-4-(2-pyrrolidin-1-ylethoxy)nitrobenzene (V.1.a) is dissolved in 100 mL of methanol and hydrogenated with hydrogen and 200 mg of Raney nickel as catalyst until the reaction is complete. Then the catalyst is filtered off and the solvent is eliminated. Yield: 1.43 g (97% of theory); Rf value: 0.15 (silica gel, methylene chloride/methanol/ammonia=9:1:0.1); C14H20N2O3; EII mass spectrum: m/z=265 [M+H]+.

Workup

  1. filtrationThen the catalyst is filtered off

Sources & evidence

ORD record
ord-8a80548ee0004761a115aecb4616e6a8
Source dataset
uspto-grants-2009_10
Patent number
US07605176B2

Reaction notes

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